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8 dates in 8 days

Where do I begin? In the last eight days, I have gone to four restaurants, two coffee shops and a handful of bars with eight different men. All of them first dates. As someone who’s been in one relationship or another for half of my years, I can honestly say that the last week has comprised the most dating of my life.

When it comes to me and men, I either know what I want, or don’t have a clue, the latter being the stronger tendency. This is what drove me to the world of online dating. And my experiment started with a valuable exercise: In 4,000 words or less, I had to write a bio explaining my personality and what I truly wanted. The lengthy piece I drafted included both an upfront appraisal of myself—“I don’t look or act my age. Eh, I could be in better shape, for sure”—and a detailed description of my ideal man—“I want strong arms that I can melt into. I want hair on your head (preferably not colored—gray is okay), but not much anywhere else.”

Sure, it’s specific, but I was curious what responses I’d get if I wrote the most honest profile possible. Most people appreciated it, but a couple of users didn’t find my preferences insightful. “The man you’re looking for doesn’t exist!” they wrote, or, “You’re too picky!” My response: Why settle?

In the bio, I talked about wanting “to be taken care of for once,” so I chose an older doctor for Date No. 1. His online correspondence seemed heartfelt, and we landed on plans for dinner at Marrakech. “That’s perfect,” he said, “I actually studied Moroccan music.” His studies kept the conversation going, as he identified which songs were and were not actually Moroccan, and even roped the server into the discussion, speaking to him in Egyptian Arabic. Pretty impressive.

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Surprisingly, he was too shy to tip the restaurant’s belly dancer, so I took his dollar and added it to her undulating hips myself. Even more surprising, he wasn’t too shy to stroke my hands. When I said that I didn’t take care of them, he responded, “That’s okay; I’ll take care of them for you.”

Date No. 2 wasn’t a selection based on deep thought: He won me over with a humble one-liner and offerings of sushi, my favorite food. I combed through his profile for reasons to reject him—a mustache, pictures with babies, pictures with dogs, not capitalizing “I,” being too short, too old, too young, too muscular, too “Ed Hardy,” or too scummy—but No. 2 passed muster, so we made a plan: 6:30 p.m., tapas, Downtown.

When we finally found each other among a crowd of tourists on Fremont Street and arrived at our destination, Firefly at the Plaza was closed. I like a man in charge, so I told him to pick any place in the neighborhood. I was afraid I’d be doomed to $1 hot dogs or $5.99 prime rib, but he led me through the Golden Nugget to Chart House, an aquamarine seafood haven. As we shared several small plates, conversation and laughs flowed. I made fun of his drinking pink champagne, he taught me that Japanese people are the “tastiest,” according to cannibals, and even referenced my lengthy online profile. “You mentioned that you wanted strong arms … So, can I stop flexing now? Because mine are getting really tired.”

While the men were friendly, the first few dates were nerve-racking. I worried whether I’d be able to be myself, whether I’d be rejected, whether these strangers would invade my space or cross my boundaries. I worried they’d show up with some unforeseen oddity that had landed them on a dating site in the first place. Then again, I was on there, too.

Date No. 3 was kind of cheating. Technically, I met the out-of-town pilot at karaoke a couple of months ago, and he arranged a night off in Vegas to take me out. We grabbed dinner, then headed back to karaoke at Ellis Island, where we’d first met. The woman next to us at the bar told us we were going to get married, before filling us in on her woeful story of unrequited love. The pilot didn’t sing, but he complimented my performance sweetly, even though I trembled all through “Love is a Battlefield.” I left him at hotel check-in, not knowing when or if we’d see each other again.

Despite my hesitance to date out-of-state, I agreed to go out with Date No. 4, an entrepreneur who was escaping the East Coast for the winter. He suggested coffee at Nordstrom’s eBar at Fashion Show Mall, since it was very public and therefore safe for meeting strangers. At first glance he said, “You look exactly like your pictures,” which I took as a compliment. An hour or so later, he changed his mind. “Actually,” he said, “you look much better in person than in your pictures.” And then he blushed.

We talked and talked. Or rather, he talked and talked while I sat and listened shyly. He was the second date to acknowledge that he was telling me much more than usual, and I assured him that I was used to it. We shared pictures of our cats as the Tommy Bahama fashion show emerged from the ground behind us for the third time.

I broke my “no looking for 18-year-olds” rule with Date No. 5, because the high end of his age range was listed at 120, which I figured would average out. He seemed like someone I would get along with, down to agreeing with my fashion sense and loving Trader Joe’s, and we decided on cocktails at the Griffin. It was a freezing cold night, and the fireplaces were most welcoming. In spite of common ground, the conversation didn’t come easily. Staring at a fire doesn’t add much spark to the interview process of a date, which by then had officially become what I hated most about dating. Eventually I dragged him next door to Don’t Tell Mama, where at least we would be entertained.

I’d been a nervous wreck at first, but after Date No. 5, I snapped out of it, relaxed and stopped making such a fuss in my head. I stopped thinking of the meetings as “dates,” and started thinking of them as two people going to grab coffee, drinks or lunch.

I agreed to Date No. 6 because he was not my type. I wanted to challenge myself to not write someone off so quickly. He was handsome and fit, but more of an outdoorsman than an urbanite, and the rescue dog that I wasn’t crazy about seeing in his pictures was waiting in his car when he met me at the bookstore coffee shop (where he did not drink coffee and we did not look at books). We did talk through the whole visit, so I could be corny and say that our lives were the only open books necessary. And I did pet his dog. I love animals; I’m just not a “dog person.” They’re too much like kids, and I do not want kids.

By the time I asked out Date No. 7, I had hit my stride. I’d planned to go out by myself to the Wynn bar where I like to drink coffee and eat its addictive snack mix, so I simply invited him along. Online, he seemed funny and down-to-earth, and joked about whether he had to ditch his Ed Hardy shirt before our date (thankfully, he had none).

When he showed up, I met a strapping younger man with more career goals and standard life accomplishments than me, the older woman. We readily agreed that the dating “interview” sucked, and once that was thrown out the window, we were just two people hanging out, having a good time.

Date No. 8 was running late. “Our date could just consist of us on the phone while I drink my beer here and you’re stuck in your car,” I joked over the phone from Gordon Biersch. The warm sun shone through the bar’s windows, the air was thick with delicious smells from the kitchen, and the crafted brews were welcome and refreshing. Conversation was easy; I high-fived him for landing a job with the FBI (though I didn’t ask what specifically he did), and we decided to share two dishes for a good, bonding lunch. And if I may say so without compromising his masculinity (“I do about 120 push-ups every morning just to get my blood flowing.”), it didn’t hurt that he was pretty.

I ended my eight-night extravaganza feeling optimistic. If I could luck out with several guys in a row who were all so sweet, attractive and willing to put up with the demands of my honestly written profile, then maybe this dating world isn’t so scary or disappointing after all. I was asked for second dates by seven out of the eight, and more than half of them I’d be willing to meet again. Those are pretty good odds!

Heading online is a good choice for someone looking for a mate, or just curious to see what reaction they’d get if they were totally upfront about what they want and who they are. In the real world, dating is full of games that—while not eliminated completely—can be significantly axed by honest online dating. Some people will tell you you’re too picky. But when you’ve got thousands of other online users to choose from there’s only one question: Why settle?